Yes, those are all problems with asking why and usually show up in a bad environment. Even with all that said, it's the most important question. Your list is a

Yes, those are all problems with asking why and usually show up in a bad environment. Even with all that said, it's the most important question. Your list is a great example as to why having a toxic work environment will kill innovation; because people are afraid to ask and understand, "why." 1. The "how" is often formed by the "why," as in "why are we writing this software?" What problem are we solving? If you can't answer this well, the "how" is irrelevant. Don't get me wrong, the "how" is important too, but the "how" is dependent on the why. 2. I agree some people are dicks about it. The best way to counter that is have a good answer to the "why," then ask the person if they have anything to add. If they are just doing it to be a prick, they usually don't have an answer, or come up with something stupid. If they have actually been thinking about it, they might contribute something you haven't thought of, and you'll just have to deal with their abrasiveness to get it. 3. You absolutely need to think about your "why." If you don't have a complete answer, then say so, but add that you are still "chewing on it." It is intimidating, that's why you should always have a good answer.